Chemoselective per-O-trimethylsilylation and homogeneous N-functionalisation of amino sugars

Chem Commun (Camb). 2015 Jan 4;51(1):104-6. doi: 10.1039/c4cc06645f.

Abstract

A highly efficient CH3CN-promoted hexamethyldisilazane per-O-trimethylsilylation of amino sugars was developed. Its applications in homogenous N-functionalisation and a concise synthesis of glucosamine 6-phosphate are described.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetonitriles / chemistry
  • Amino Sugars / chemistry*
  • Glucosamine / analogs & derivatives
  • Glucosamine / chemical synthesis
  • Glucosamine / chemistry
  • Glucose-6-Phosphate / analogs & derivatives
  • Glucose-6-Phosphate / chemical synthesis
  • Glucose-6-Phosphate / chemistry
  • Nitrogen / chemistry
  • Organosilicon Compounds / chemistry
  • Oxygen / chemistry
  • Pyridines / chemistry

Substances

  • Acetonitriles
  • Amino Sugars
  • Organosilicon Compounds
  • Pyridines
  • glucosamine 6-phosphate
  • Glucose-6-Phosphate
  • hexamethylsilazane
  • Glucosamine
  • Nitrogen
  • pyridine
  • Oxygen